Connecticut’s largest city, Bridgeport has seen several booms in its time—from farming to whaling and, until the 1970s, manufacturing. Today’s Bridgeport, advantageously located an hour’s train ride from NYC, is a thriving service-based city with the talent and equity to prove it. The citizenry here—priced out of NYC or Boston or tempted by floorplans with a bit more elbow room—are well-educated and well-monied (ranking #6 for Educational Attainment and #5 for GDP per Capita), continuing a legacy of business savvy started by P.T. Barnum, circus mogul and former Bridgeport mayor. Healthcare, education and hospitality jobs are filling the space once occupied by manufacturing, and the city is investing in itself—attracting new residents and businesses alike while it’s at it. All eyes are on the waterfront, where Steelpointe Harbor is coming to life: a 2.8-million-square-foot development equipped with a luxe marina, public spaces and high-end living. There’s also a recent proposal for a new waterfront soccer stadium; it’s getting traction, but approval is still a ways off. Until then, the best waterfront views can be found at Seaside Park, designed by Frederick Law Olmsted and Calvert Vaux—the pair behind New York City’s Central Park. It’s a big reason Bridgeport ranks #37 in our Green Space subcategory.